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195 Lodgings in Pittsfield, MA
9.8 45 reviews
Pittsfield, MA
10/06 – 10/13
$296/nighttotal: $2072 (7 )
Berkshire Lakehouse - 3 Bedrooms - Sleeps 5
1 3
apartment , Pittsfield
This Pittsfield lake house, situated on Onota Lake with private dock access and proximity to Pittsfield's ski slopes and hiking trails, offers a perfect base for exploring the Berkshires. This three-bedroom, one-bathroom home sleeps five, features a fully equipped kitchen, laundry facilities, a large deck, fenced yard, and access to kayaks and paddleboards.
Pittsfield, MA
06/18 – 06/29
$707/nighttotal: $7777 (11 )
Berkshires Chalet Mins To Tanglewood/lenox
1 2
apartment , Richmond
This Richmond rental is located approximately 4 miles from Tanglewood and offers convenient access to Berkshire attractions, including skiing, swimming, boating, hiking, summer theater, and dining. This 4-bedroom, 3-bathroom apartment accommodates up to 10 guests and features a new kitchen with stainless steel appliances, a screened porch, central air conditioning, and a covered outdoor hot tub.
10 7 reviews
Pittsfield, MA
06/18 – 06/29
$280/nighttotal: $3080 (11 )
Scroll No More - Your Magical Lenox Place
3 2
apartment , Lenox
This ranch-style home is located just minutes from downtown Lenox, placing you close to shops, restaurants, and cultural attractions. It has received excellent ratings for location, cleanliness, and overall experience. This 3-bedroom home comfortably accommodates up to 4 guests. Enjoy amenities like a fireplace, a jacuzzi, a garden, and mountain views, making it perfect for a relaxing getaway.
9.9 26 reviews
Pittsfield, MA
07/01 – 07/31
$302/nighttotal: $9060 (30 )
Condo On The Mountain
1 1
apartment , Hancock
This apartment is located within the renowned Jiminy Peak Resort, providing easy access to skiing, snowboarding, and other winter activities. It boasts stunning views of the ski slopes, creating a captivating ambiance for guests. The apartment has received excellent ratings for its location, cleanliness, and amenities. It offers three levels with multiple bedrooms and bathrooms, providing ample space and privacy for up to six guests. The apartment includes a fully equipped kitchen, a cozy living room, a washer, dryer, and a smart TV for streaming entertainment. Guests also receive a complimentary gift certificate to explore the local country store for dining options.
10 3 reviews
Pittsfield, MA
10/06 – 10/13
$195/nighttotal: $1365 (7 )
Cozy Escape To The Berkshires
1 3
apartment , Pittsfield
This Southeast Pittsfield rental is situated in a quiet neighborhood perfect for walks, offering convenient access to the Berkshires' museums, music venues, theaters, skiing, and hiking. This two-bedroom, one-bathroom suite accommodates up to four guests and features a fully stocked kitchen, a king-sized bed, a queen-sized bed, a walk-in shower, an in-unit washer and dryer, keyless entry, and Smart TVs.
9.6 85 reviews
Pittsfield, MA
10/06 – 10/13
$478/nighttotal: $3346 (7 )
Beautiful Waterfront Home With Deep Water Dock On Onota Lake. Huge Covered Deck.
3 3
apartment , Pittsfield
This waterfront vacation home on Onota Lake in Pittsfield offers direct access to water sports and is located within 3 miles of Tanglewood Music Center, Crane Museum of Papermaking, and Colonial Theater, with Bousquet Ski Area just 2 miles away. This 1800 square foot house features 3 bedrooms, 2 bathrooms, sleeps 10, and includes a modern kitchen with a fridge, microwave, and dishwasher, plus a private dock and a large covered deck for outdoor enjoyment.
Pittsfield, MA
06/20 – 06/27
$2110/nighttotal: $14770 (7 )
Brookside Mountain Retreat By Avantstay
13 2
house , East Nassau
This Brookside Mountain Retreat is located in Hancock, East Nassau, 18 miles from Tanglewood Musical Center and Tanglewood, and 23 miles from Rensselaer Polytechnic Institute. This 6,490 square foot house accommodates up to 44 guests with 1 bedroom and 12 bathrooms, featuring a heated outdoor swimming pool, hot tub, game room, and fire pit, with amenities including a fully equipped kitchen, WiFi, and parking.
10 5 reviews
Pittsfield, MA
10/06 – 10/13
$197/nighttotal: $1379 (7 )
Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield!
2 3
apartment , Pittsfield
This centrally located bungalow in Pittsfield is just minutes away from popular attractions such as Bousquet Ski Resort, hiking trails, museums, and Tanglewood in Lenox. It offers easy access to urban amenities, and has been rated as "excellent" by previous guests. The bungalow has a floor area of 1000 square feet and can accommodate up to 5 guests. It has 2 bedrooms, 1 bathroom, a kitchen with a fridge, microwave oven, and dishwasher, and air conditioning. The bungalow also features a spa, an outdoor deck, a yard with games and a grill, and convenient access to hiking trails and museums.
10 65 reviews
Pittsfield, MA
10/06 – 10/13
$162/nighttotal: $1134 (7 )
Comfy Quaint Tavern
1 3
apartment , Pittsfield
This one-bedroom apartment is located in the southeast section of Pittsfield, a residential neighborhood within walking distance of restaurants and a seasonal ice cream shop. The apartment has received excellent ratings for cleanliness and user experience, along with a very good rating for location. The apartment features a queen-size bed in the bedroom and a queen-size pull-out couch in the living room, comfortably accommodating up to three guests. Guests can enjoy modern amenities like a full kitchen, air conditioning, and off-street parking, as well as a unique 12-foot bar with 5 stools for relaxation and socializing.
10 17 reviews
Pittsfield, MA
07/01 – 07/31
$246/nighttotal: $7380 (30 )
Berkshire Cabin
1 1
apartment , East Nassau
This East Nassau cabin, nestled in the Berkshires, is seven miles from Jiminy Peak Ski Resort and a short drive from Lenox, Pittsfield, Great Barrington, Mount Greylock State Reservation, and Tanglewood. The one-bedroom, one-bathroom cottage sleeps two, features a chef's kitchen with Wolf and Sub-Zero appliances, and offers access to hiking, snowshoeing, apple/pumpkin picking, and nearby cultural attractions.
Pittsfield, MA
08/08 – 08/15
$443/nighttotal: $3101 (7 )
New Built - Split Level House In The Berkshires
1 2
apartment , Lanesborough
This 3-bedroom, 3-bathroom Lanesborough rental is a newly built house offering 8 guests a peaceful retreat, located just a 3-minute walk to Pontoosuc Lake and a short drive from Jiminy Peak and downtown Pittsfield. This pet-friendly home features air conditioning, internet, a kitchen, and parking with EV charging, serving as an ideal base for exploring the Berkshires' numerous outdoor activities and cultural attractions.
9.9 58 reviews
Pittsfield, MA
10/06 – 10/13
$313/nighttotal: $2191 (7 )
Marie’s Place Unit 3
1 3
apartment , Pittsfield
This charming colonial house is located on a quiet street in southeast Pittsfield, just minutes from restaurants, shops, and major attractions like Hancock Shaker Village, MASS MoCA, and the Colonial Theatre. The home has consistently received excellent ratings for its cleanliness, location, and overall guest experience. The three-bedroom house comfortably accommodates up to six guests, offering a spacious living room with a gas stove, a well-equipped kitchen, and a private backyard with a deck. Enjoy amenities like air conditioning, free Wi-Fi, and parking, making this a perfect base for exploring all that Pittsfield has to offer.
Choose the Right Family Lodgings in Pittsfield, MA
These family-friendly lodgings in Pittsfield, MA offer plenty of room and keep city attractions within easy reach; find the perfect fit for your group.
9.5 37 reviews
Pittsfield, MA
10/06 – 10/13
$175/nighttotal: $1225 (7 )
Spacious 2 Bedroom Downtown Very Nice Area!
1 3
apartment , Pittsfield
This Pittsfield apartment rental is centrally located, a 5-minute walk from downtown's main street, offering easy access to numerous cafes, restaurants, shops, and a movie theater. The two-bedroom, one-bathroom unit comfortably sleeps four guests and includes amenities such as air conditioning, internet, and parking.
9.2 5 reviews
Pittsfield, MA
07/01 – 07/31
$184/nighttotal: $5520 (30 )
Gorgeous Mountain View Suite Ski On/off At Jiminy
1 1
apartment , Hancock
This upscale, renovated suite at the Country Inn is located at the base of Jiminy Peak Mountain in Hancock, Massachusetts, offering ski-in/ski-out access in winter and proximity to summer activities like the alpine slide and mountain coaster. This one-bedroom, one-bathroom condo sleeps four guests comfortably with a king bed and queen pull-out sofa, a kitchenette including a Keurig and air fryer, plus access to a heated outdoor pool, hot tubs, and a fitness center.
10 6 reviews
Pittsfield, MA
10/06 – 10/13
$988/nighttotal: $6916 (7 )
Huge Designer House On 2 Acres Property, Minutes To Restaurants, Museums
1 3
apartment , Lenox
This Lenox designer retreat, a 3-bedroom, 2-bathroom apartment, is nestled in a secluded wooded setting with immediate access to hiking trails, yet a short 5-minute drive from Lenox town center, offering easy access to festivals, museums, theaters, restaurants, and grocery stores, as well as Mabel Lakes and a nearby ski mountain. This 2,500-square-foot rental boasts a fully equipped kitchen, spacious sunroom, large-screen movie system, strong internet, a saltwater pool, Finnish sauna, and ample outdoor space on a two-acre property, comfortably accommodating families or groups.
Pittsfield, MA
10/06 – 10/13
$263/nighttotal: $1841 (7 )
Views! 2mi2ski+dtw! Great 1br Openlr/dr/kit! Fp,hpool,htub,gym,petsok,evchg!
1 3
apartment , Pittsfield
This apartment is centrally located in Pittsfield, 0.2 miles from Bousquet Ski Area and minutes from downtown Pittsfield, Tanglewood, MassMoCA, and The Mount. This pet-friendly, family-friendly condo offers 1 bedroom, 1 bathroom, and sleeps 4, featuring a full kitchen, air conditioning, and access to an indoor swimming pool, hot tub, fitness center, game room, and EV charging stations.
Best Pittsfield, MA lodging with a pool
Among the 195 accommodations in Pittsfield, MA, here are the 4 best ones with a pool
8.2 6 reviews
Pittsfield, MA
06/20 – 06/27
$388/nighttotal: $2716 (7 )
Cozy Cabin In The Berkshire Resort
2 2
cabin , Hancock
This Hancock, Massachusetts mountain home is part of a resort, conveniently located approximately 20 miles from both Tanglewood and the Cranwell Spa & Golf Club. This 9150-square-foot vacation rental boasts two bedrooms, two bathrooms, and sleeps eight, featuring a fully equipped kitchen, hot tub, private patio, fitness center access, a pool, and a jacuzzi, plus free Wi-Fi and parking.
10 3 reviews
Pittsfield, MA
07/01 – 07/31
$213/nighttotal: $6390 (30 )
Gorgeous Mountain View Suite Ski On/off At Jiminy - Fully Redone Decor
1 1
apartment , Hancock
This slopeside Hancock rental is located within two miles of Jiminy Peak Mountain Resort, the Alpine Super Slide, and the Mountain Coaster, offering convenient access to popular attractions. This 500-square-foot apartment features two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, in-unit laundry, a private pool, and access to a shared indoor pool and fitness center.
9.8 22 reviews
Pittsfield, MA
07/01 – 07/31
$228/nighttotal: $6840 (30 )
Deluxe Yeti Suite On Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
1 1
apartment , Hancock
This ski-in/ski-out apartment is nestled in the mountains of Hancock, just 0.1 miles from Jiminy Peak Mountain Resort and within 9 miles of Zema's Nursery and Pittsfield State Forest. It has an excellent user rating. The apartment has 1 bedroom, 1 bathroom, and a floor area of 500 square feet. It can accommodate up to 4 guests. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a fitness center, and parking. Activities and features include ski-in/ski-out access, an indoor pool, a fitness center, a fireplace, a DVD player, a refrigerator, and a dryer.
10 45 reviews
Pittsfield, MA
10/06 – 10/13
$657/nighttotal: $4599 (7 )
Lenox Grand Colonial With Pool By Evergreen Home
1 3
apartment , Lenox
This spacious Lenox house, located on a quiet cul-de-sac ten minutes from downtown Lenox and Tanglewood, offers convenient access to shops, restaurants, and numerous Berkshire attractions. The 3000-square-foot, four-bedroom home comfortably sleeps eight, boasting a private pool, extensive backyard, fully equipped kitchen, and in-home entertainment options including a ping pong table, all within a short drive of Mass MoCA, the Red Lion Inn, and various wineries and ski resorts.
Frequently Asked Questions about accommodations in Pittsfield, MA
What are the top attractions and must-see sites in Pittsfield, MA?
You definitely want to check out the Berkshire Museum, it has a great collection of art and history. The Clark Art Institute is also a must-see, they have an amazing collection of Impressionist and early modern art, and the grounds are beautiful. And don't forget about the Barrington Stage Company, they put on some great shows throughout the year.
What are the best accommodations in Pittsfield, MA?
Which cultural festivals and seasonal events should visitors attend in Pittsfield, MA?
The biggest event is the 10 Days of Summer festival in July, it's a great way to experience local music and art. You should also check out the Pittsfield Farmers Market on Saturdays, it's a great place to get fresh produce and local crafts. And if you're in town during the fall, you can't miss the foliage, it's absolutely stunning.
What are the best accommodations with a pool in Pittsfield, MA?
What are the most convenient modes of transportation within Pittsfield, MA?
Pittsfield is pretty walkable, especially downtown. You can also take the bus, the Berkshire Regional Transit Authority has routes throughout the city. If you're planning on exploring the surrounding area, renting a car is your best bet.
What are the best accommodations with a jacuzzi in Pittsfield, MA?
What outdoor activities and adventures are popular in and around Pittsfield, MA?
There's plenty to do outdoors in Pittsfield. You can hike or bike the Appalachian Trail, go kayaking on Lake Onota, or visit the nearby Mount Greylock State Reservation, the highest point in Massachusetts. You can also check out the Taconic Crest Trail, which runs along the Taconic Mountains.
What are the best accommodations for families and kids in Pittsfield, MA?
What types of accommodations are available in Pittsfield, MA?
You can find everything from budget-friendly motels to upscale hotels in Pittsfield. There are also a few bed and breakfasts and vacation rentals available. You can also find some great places to stay in the nearby towns of Lenox and Stockbridge.
What are the best pet friendly accommodations in Pittsfield, MA?
The best time to visit Pittsfield is in the fall, when the leaves change color. It's also a great time to visit in the summer, when the weather is warm and there are lots of outdoor activities to enjoy. You can find some great deals on accommodations during the shoulder seasons, too.
What are the best accommodations with parking in Pittsfield, MA?
What local dishes and culinary experiences are a must-try in Pittsfield, MA?
You have to try the Berkshire pork. It's a local specialty, and there are plenty of restaurants in Pittsfield that serve it. You should also check out the local breweries, they're making some really great craft beers. You can also find some great Italian food in Pittsfield, it's a popular cuisine here.
In which part of Pittsfield, MA should you consider renting accommodation?
Downtown Pittsfield is a good choice, it's close to all the action and has a good selection of restaurants and shops. If you're looking for something quieter, you might want to consider staying in the nearby town of Lenox, which is known for its beautiful scenery and charming shops.
Destinations nearby
Best Pittsfield, MA accommodation with a garden
9.9 100 reviews
Pittsfield, MA
10/06 – 10/13
$641/nighttotal: $4487 (7 )
Renovated Pittsfield Colonial By Evergreen Home
4 3
apartment , Pittsfield
This Pittsfield apartment is in the heart of the Berkshires, surrounded by museums, theaters, and hiking trails. It has excellent user, location, and cleanliness ratings. The apartment has 4 bedrooms, 3 bathrooms, and a bonus room, with a floor area of 3900 square feet. It can accommodate up to 12 guests. The kitchen has new appliances, and there's a large deck overlooking a private backyard and woods. Other amenities include Wi-Fi, a washer and dryer, a fitness center, and parking.
9.6 33 reviews
Pittsfield, MA
08/08 – 08/15
$147/nighttotal: $1029 (7 )
Available For Healthcare And Long Term Stays Welcome 3 Miles From Hospital
1 2
apartment , Lanesborough
This Lanesborough, Massachusetts apartment rental is conveniently located on Route 7, a half-mile north of the Pittsfield city line, offering easy access to Lake Pontoosuc and Mount Greylock State Reservation (a 15-20 minute drive). The 600-square-foot, pet-friendly unit features one bedroom, one bathroom, a full kitchen, and outdoor amenities including a yard, grill, and fire pit, comfortably accommodating up to four guests with a king-size bed, daybeds, and a futon.
9.6 37 reviews
Pittsfield, MA
10/06 – 10/13
$225/nighttotal: $1575 (7 )
Petite Paris
1 3
apartment , Pittsfield
This Pittsfield apartment rental, perfect for families, is located in a quiet neighborhood—the exact address is undisclosed, but proximity to local landmarks is implied. The three-bedroom, one-bathroom unit sleeps six guests and includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and a garden.
9.9 210 reviews
Pittsfield, MA
10/06 – 10/13
$305/nighttotal: $2135 (7 )
Cantabile Life In The Berkshires
1 3
apartment , Pittsfield
This apartment is located in a quiet, friendly neighborhood in Pittsfield, just minutes from several lakes, mountains, and attractions like Tanglewood and Bousquet Ski Area. It boasts excellent ratings for location, cleanliness, and user satisfaction. The rental offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the spacious living areas, well-equipped kitchen, and outdoor space, plus family-friendly amenities like games, a piano, and child-friendly equipment.
Neighborhoods and points of interest in Pittsfield, MA
Best Pittsfield, MA accommodation with a kitchen
8.8 1678 reviews
Pittsfield, MA
10/06 – 10/13
$168/nighttotal: $1176 (7 )
Berkshire Mountain Lodge
1 3
house , Pittsfield
Located in Pittsfield, this chalet is close to Guido's Marketplace and within 3 miles of attractions such as Bousquet Ski Area and Housatonic River. With a very good user rating and an excellent location rating, this chalet offers a comfortable stay for travelers. The chalet features one bedroom and one bathroom, and includes a kitchen with a fridge, microwave oven, and dishwasher. Guests can enjoy amenities such as air conditioning, a swimming pool, a Jacuzzi, a garden, a sauna, a spa, a concierge, a restaurant, a bar, a fitness center, and parking.
10 1 review
Pittsfield, MA
08/08 – 08/15
$212/nighttotal: $1484 (7 )
Charming 1 Bedroom - 4 Star Resort W/ Heated Pool, Gym, Wi-fi, Lot's More!
1 2
resort , Pittsfield
The Berkshire Mountain Lodge is located in Pittsfield, Massachusetts, close to Lenox and within easy reach of attractions like Tanglewood and The Mount. This charming resort provides a comfortable and convenient base for exploring the Berkshires. The "Charming 1 Bedroom - 4 Star Resort W\/ Heated Pool, Gym, Wi-fi, Lot's More!" offers one-bedroom units that can accommodate up to four guests. Each unit is equipped with modern amenities, including a full kitchen, a cozy living area, and a dining space, as well as access to a heated pool, a gym, and Wi-Fi.
10 3 reviews
Pittsfield, MA
07/01 – 07/31
$184/nighttotal: $5520 (30 )
Must See Cabin Suite Jiminy Sleeps 4- Mountainview
1 1
apartment , Hancock
This Hancock, Massachusetts condo is located directly on Jiminy Peak Mountain, providing ski-in/ski-out access in winter and immediate access to hiking trails in summer, plus proximity to Jiminy Peak Mountain Resort's Adventure Park. The fully renovated one-bedroom suite sleeps four with a king bed, queen sofa bed, kitchenette (including a Keurig), two TVs, and access to Jiminy Peak's year-round heated pool, hot tubs, and fitness center.
10 3 reviews
Pittsfield, MA
07/01 – 07/31
$307/nighttotal: $9210 (30 )
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
1 1
apartment , Hancock
This Hancock condo is located in the Village Center of Jiminy Peak Mountain Resort, directly across from the main ski lift, providing ski-in/ski-out access. The 650-square-foot unit sleeps four, features a fully equipped kitchen with a Keurig and air fryer, and offers access to a year-round heated pool, hot tubs, and a fitness center.
